US3925462A - Wash-durable antistatic agent - Google Patents

Wash-durable antistatic agent Download PDF

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Publication number
US3925462A
US3925462A US319745A US31974572A US3925462A US 3925462 A US3925462 A US 3925462A US 319745 A US319745 A US 319745A US 31974572 A US31974572 A US 31974572A US 3925462 A US3925462 A US 3925462A
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cationic surfactant
group
composition
diisocyanate
blocking agent
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Expired - Lifetime
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US319745A
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English (en)
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Kenneth W Graff
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Zeneca Inc
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ICI Americas Inc
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Priority to US319745A priority Critical patent/US3925462A/en
Priority to JP744801A priority patent/JPS5239480B2/ja
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/461—Quaternised amin-amides from polyamines or heterocyclic compounds or polyamino-acids
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/372—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
    • D06M15/568—Reaction products of isocyanates with polyethers

Definitions

  • ABSTRACT Disclosed are textile treating compositions comprising a novel class of carbamic acid esters containing at least one thermally labile carbamic acid ester group and containing at least one thermally stable carbamic acid ester group derived from a cationic surfactant represented by the generalized fonnula wherein rz represents an integer from 2 to 4, x represents a number from O to 100, y represents a number from 0 to 100, R represents a radical selected from the group consisting of alkyl and alkenyl radicals containing from 6 to 22 carbon atoms, R' represents a radical selected from the group consisting of alkyl and hydroxyalkyl radicals containing from 1 to 5 carbon atoms, and X represents an anion.
  • rz represents an integer from 2 to 4
  • x represents a number from O to 100
  • y represents a number from 0 to 100
  • R represents a radical selected from the group consisting of alkyl and alkenyl radicals containing from
  • the present invention relates to textile treating compositions, to methods of treating textiles and to the textiles having improved physical properties. More particularly, the present invention relates to novel carbamic acid esters which are useful for treating textile materials to impart antistatic properties.
  • novel carbamic acid esters of the present invention may be prepared by reacting, simultaneously or consecutively in any order, an aromatic polyisocyanate, a cationic surfactant as defined below, and a thermally reversible blocking agent, such as phenol, methylphenol, dimethylphenol, trimethylphenol, ethylphenol, and mixtures thereof.
  • a thermally reversible blocking agent such as phenol, methylphenol, dimethylphenol, trimethylphenol, ethylphenol, and mixtures thereof.
  • the polyisocyanate may be reacted with the blocking agent in such proportion that l-NCO group remains and may subsequently be reacted with the cationic surfactant.
  • cationic surfactant As used hereinabove and hereinafter in the present specification is intended cationic surfactants represented by the general formula wherein n represents an integer from 2 to 4, x represents a number from to 100, y represents a number from 0 to 100, R represents a radical selected from the group consisting of alkyl and alkenyl radicals containing from 6 to 22 carbon atoms, R represents a radical selected from the group consisting of alkyl and hydroxyalkyl radicals containing from 1 to 5 carbon atoms, and X represents an anion.
  • the amounts of cationic surfactant compound, polyisocyanate, and blocking agent used are selected to assure that the resulting carbamate contains at least one thermally stable carbamate group derived from the subject cationic surfactant compounds, at least one thermally labile carbamate group derived from the blocking agent and no free isocyanate groups. This may be accomplished by reacting the polyisocyanate, blocking agent, and cationic surfactant compound in such proportions that the ratio of mols of blocking agent to NCO groups is less than one and the number of NCO groups is equal to or less than the sum of the hydroxyl groups from the cationic surfactant compound and mols of blocking agent.
  • one mol of the cationic surfactant compound containing two hydroxyl groups and two mols of a diisocyanate may be reacted with two mols of blocking agent whereas one mol of the cationic surfactant compound containing two hydroxyl groups and two mols of triisocyanate may be reacted with four mols of a blocking agent.
  • the reaction is carried out under conditions which exclude moisture and preferably in the substantial absence of oxygen to minimize the discoloration of the resulting carbarnic acid ester. Temperatures up to 200C. may be used. Preferably, the reaction is carried out at temperatures within the range of about 50C. to l60C.
  • the present reaction is generally carried out at atmospheric pressure; however, suitable reduced pressure may be used when indicated.
  • the reaction may be conducted in the absence of a solvent or in the presence of a suitable amount of a solvent which is inert to the isocyanate groups. If a solvent is used, the quantity generally utilized is such to dissolve the reactants. [llustrative examples of such solvents include benzene and l,l,l-trichloroethane.
  • a catalytic amount of a catalyst selected from the group consisting of aliphatic tertiary amines, alkali or alkaline earth metal oxides, carbonates, alcoholates, and phenates and metal salts of carboxylic acids may be used to facilitate the reaction.
  • a catalyst selected from the group consisting of aliphatic tertiary amines, alkali or alkaline earth metal oxides, carbonates, alcoholates, and phenates and metal salts of carboxylic acids may be used to facilitate the reaction.
  • a catalyst selected from the group consisting of aliphatic tertiary amines, alkali or alkaline earth metal oxides, carbonates, alcoholates, and phenates and metal salts of carboxylic acids may be used to facilitate the reaction.
  • a catalyst selected from the group consisting of aliphatic tertiary amines, alkali or alkaline earth metal oxides, carbonates, alcoholates, and phenates and metal salts of carboxylic acids may
  • the polyisocyanates which may be used to prepare the carbamic acid ester of this invention are aromatic polyisocyanates; that is, isocyanates containing at least two NCO groups directly attached to carbon atoms of an aromatic ring.
  • aromatic polyisocyanates which may be used to prepare the carbarnic acid esters of this invention include 2,4-toluene diisocyanate; 2,6-toluene diisocyanate; phenylene diisocyanate; methoxyphenylene 2,4-diisocyanate', diphenylmethane 4,4'-diisocyanate; 3-methyldiphenylmethane 4,4'-diisocyanate; diphenylether 2,4,4'-triisocyanate; and mixtures thereof.
  • the preferred isocyanate is 2,4-toluene diisocyanate.
  • the cationic surfactant compound used to prepare the subject antistatic agents is one characterized by the following general formula wherein n represents an integer from 2 to 4, x represents a number from to 100, y represents a number from 0 to 100, R represents a radical selected from the group consisting of alkyl and alkenyl radicals containing from 6 to 22 carbon atoms, R represents a radical selected from the group consisting of alkyl and hydroxyalkyl radicals containing from 1 to carbon atoms, and X represents an anion.
  • a preferred class of cationic surfactants is characterized by the foregoing generalized formula wherein the sum of x and y is a number from 5 to 50.
  • Alkyl and alkenyl radicals represented by R include such typical radicals as hexyl, octyl, nonyl, decyl, dodecyl. stearyl, oleyl, linoleyl, palmityl, behenyl, lionlenyl, and the like.
  • Alkyl radicals represented by R typically include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-amyl, isoamyl, sec-amyl, t-amyl, and other isomeric amyl radicals.
  • Hydroxyalkyl radicals represented by R are exemplified by hydroxyethyl, hydroxypropyl, hydroxyisopropyl, dihydroxypropyl. hydroxybutyl, dihydroxybutyl, hydroxymethyl, dihydroxyamyl, and the like.
  • Anions typical of those represented by X- are the chloride, bromide, fluoride, iodide, sulfate, sulfonate, phosphate, phosphite, cyanate, isocyanate, sulfite, bisulfite, nitrate, nitrite, oxalate, silicate sulfide, acetate, ethyl sulfate, and other common inorganic and inorganic ions.
  • Quaternary salts of ethoxylated fatty amines of the kind described above are well known, many are commercially available, and all may be prepared by means of conventional chemical reactions and procedures from primary amines.
  • R represents a radical selected from the group consisting of alkyl and hydroxyalkyl radicals containing from 1 to 5 carbon atoms
  • n represents an integer from 2 to 4
  • 1: represents a number from 0 to 100
  • y represents a number from 0 to 100
  • R represents a radical selected from the group consisting of alkyl and alkenyl radicals containing from 6 to 22 carbon atoms
  • A represents an organic aromatic polyisocyanate such as disclosed hereinabove
  • B represents a phenolic thermally reversible blocking agent such as disclosed hereinabove
  • X represents an anion.
  • R of the cationic surfactant used as a reactant to prepare the subject carbamic acid ester is hydroxyalkyl
  • monophenoLblocked organic polyisocyanates (A-B) also attached at this position.
  • EXAMPLE 1 454 Grams of phenol were refluxed for about 2 hours in 200 ml. of benzene to remove about 3 ml. of water in a Dean-Stark trap. Then the solvent was vacuum stripped at 80C/0. mm Hg until crystals of phenol appeared in the condenser. Vacuum stripping was continued at about 85C.l0.5 mm Hg and then the product was allowed to cool. The vacuum stripped phenol (426.4 grams) was then treated dropwise rapidly at 150C. with 792 grams 2,4-toluene diisocyanate. Heating was continued for 2 hours at 150C. Then the product was cooled to give a slightly hazy yellow viscous monophenol-blocked toluene diisocyanate.
  • EXAMPLE 2 288 Grams of diethyl sulfate quaternary salt of polyoxyethylene(20) hydrogenated tallow amine and 4.35 grams aqueous sodium hydroxide (to neutralize 90% of the acid in the quaternary salt) were stirred into 300 grams l,l,l-trichloroethane. The solution was azeotroped to remove water at 77-81C. with periodic addition of more 1,1,l-trichloroethane until no more water could be removed. Then the solution was cooled to give a clear red-brown product.
  • EXAMPLE 3 610 Grams of diethyl sulfate quaternary salt of polyoxyethylene( 20 )hydrogenated tallow amine (neutralized and azeotroped as in Example 2) were treated with 336 grams of monophenol-blocked 2,4-toluene diisocy anate (prepared as in Example 1) dissolved in l65 ml.
  • EXAMPLE 4 By a process similar to that of Example 3, 800 grams of diethyl sulfate quaternary salt of polyoxye thylene( 20)hydrogenated tallow amine was azeotroped to remove water in toluene instead of in l,l,l-trichloroethane to give a clear solution.
  • the water-free quaternary solution was then treated with 340 grams of monophenol-blocked 2,4toluenc diisocyanate in 250 ml. of toluene at 72C. An exothermic reaction began and the temperature raised to C. over about 15 minutes. The temperature was maintained at 100C. by heating for 1.5 hours. Then the solution was allowed to cool to give 3000 grams of solution containing 56.25% solids of a carbamic acid ester of the present invention.
  • EXAMPLE 5 To 3l70 grams of diethyl sulfate quaternary salt of polyoxyethylene hydrogenated tallow amine (prepared in toluene as in Example 4) in toluene to give 4784 grams of solution was added 1392 grams of monophenol-blocked 2,4-toluene diisocyanate in 800 ml. of toluene, which was washed in with 200 ml. more of toluene. Then the reaction mixture was heated to and maintained at 80C. overnight (about 17 hours). The reaction mixture was then cooled to give 7029 grams solution containing 63.68% solids.
  • the solvent was evaporated from 46.4 grams of the above prepared solution to yield 30.0 grams of the desired carbamic acid ester textile treating product.
  • diethyl sulfate quaternary salt of polyoxyethylene( 20)hydrogenated tallow amine is principally N,N-polyoxyethylene (20)-N-ethyl-N-stearylammonium ethyl sulfate and was prepared from Armeen HTD hydrogenated tallow amine, which is manufactured by Armour industrial Chemical Company, Chicago, Illinois.
  • carbamic acid esters of the foregoing description may be used to treat textile materials to impart thereto improved physical characteristics, such as antistatic properites. It has been found that if the carbamic acid esters are applied to textile materials and then cured by heating the textile material to an elevated temperature, the carbamic acid esters become attached to the textile material so that the improved properties imparted to the textile material will not be removed by subsequent washing.
  • this invention is not limited by theoretical considerations, it is believed that the thermally labile carbamate group of the carbamic acid ester decomposes at elevated temperatures to form an aromatic NCO group and free phenol and that the aromatic NCO group then reacts with the textile material and/or other NCO groups to form thermally stable groups.
  • the carbamic acid esters of the present invention may be advantageously utilized for application to textile materials alone or in combination with a wide variety of chemical treating agents, among which are included, for example, softening compounds, emulsifying agents, wetting agents, and numerous other compounds that enhance the physical characteristics of the textile materials.
  • the textile material may be treated with the carbamic acid esters of this invention along with any of the wide variety of chemical treating agents listed above, either simultaneously or separately in any order.
  • the textile treating compositions of this invention may be applied to textile materials from aqueous medium, an organic solvent, or an emulsion of water and an organic solvent.
  • organic solvents which may be used include isopropanol, l, l ,l-trichloroethane, l l ,2-trichloroethane, perchloroethylene, benzene, carbon tetrachloride, chloroform, pentachloroethane, and dichlorobenzene.
  • Textile materials may be treated with the bath containing a textile treating composition of this invention by any suitable means, such as by immersion therein or by spraying.
  • the textile material may either be run through a padding machine where the textile material is first dipped into the bath and then squeezed, or the textile materials may be dipped into the bath and the excess liquid extracted by centrifugation.
  • the amount of carbamic acid ester applied to the textile material in accordance with the present invention may vary from about 0.3% to about l0% by weight based on the dry weight of the textile material. However, it has been determined that a more preferred range is from about 0.5% to about 5% by weight based on the dry weight of the textile material in view of the results obtained and cost of material.
  • the textile material having the carbamic acid ester thereon It is necessary to subject the textile material having the carbamic acid ester thereon to an elevated temperature in order to initiate the curing reaction between the carbamic acid ester and the textile material.
  • the particular temperature used and the duration of the heating step depends upon the nature of the textile material being treated and on the particular carbamic acid ester used. In each situation, however, the temperature and heating time are those necessary to sufficiently cause reaction of the carbamic acid ester with the textile material.
  • the heat cure may be affected at temperatures from about lOOF. and about 350F. and in periods of time ranging from about 40 to about 60 minutes at the lower temperature to about 0.5 to about 10 minutes at the higher temperature.
  • the preferred temperature is from about 300F. to 350F.
  • Textile materials which may be treated with the textile composition of this invention include any textile material conventionally treated with antistatic agents; for example, textile materials comprised of nylon and polyesters and blends of such synthetic fibers with other cellulosic and noncellulosic materials such as acrylics, rayon, cotton, linen, and mixtures thereof.
  • the textile materials that can be treated in accordance with the present invention may be in the form of filaments, fibers, threads and yarns, or in the form of woven, nonwoven, knit, or otherwise formed fabrics, sheets, and cloths.
  • EXAMPLE 6 A solution of 3 grams of the product of Example 1 and 3 grams of 1,1 ,l-trichloroethane was prepared and then dispersed in 294 grams of water having a tempe rature of about 72F. Fifteen inch by fifteen inch pieces of spun polyester fabric were then padded with the above prepared solution on a Butterworth pad using a double dip, double nip technique. The polyester fabric had a 67% wet pickup. Then the treated polyester fabric was allowed to dry overnight at room temperature of about 72F. Following this drying cycle, the treated polyester fabric was then cured in a hot air oven for 8 minutes at about 300F.
  • the test results obtained are set forth in the following table wherein the Log R is a measure of the resistance of the fabric being tested. bog R values within the range of from about ID to 13 are thought to indicate that the fabric possesses significant antistatic properties.
  • the washing of the fabrics in the above examples was accomplished with the use of a Kenmore washer, Model 600, with a 12 minute wash cycle using the commercial detergent Tide followed by 2 rinses and a spin 7 cycle. Following the above described wash procedure, the test fabrics were then dried in a Kenmore dryer for 20 minutes.
  • EXAMPLE 7 Four and a half grams of the product of Example 1 were dissolved in 4% grams of l,l,l-trichloroethane and then the resulting solution was dispersed in 291 grams of water at about 72F. Then l5 inch by inch pieces of spun polyester fabric were padded as in Example 6 followed by a drying cycle of 3 minutes at 225F. in a forced air oven and a curing cycle of 3 minutes at about 325F. The pieces of polyester fabric were then washed, conditioned, and tested as in Example 6 and the results obtained are as follows:
  • a composition consisting essentially of the reaction product of (a) an organic aromatic polyisocyanate containing at least 2 NCO groups directly attached to the carbon atoms of an aromatic ring, (b) a thermally reversible blocking agent selected from the group consisting of phenol, lower alkyl substituted phenols, and mixtures thereof, and (c) a cationic surfactant represented by the formula wherein n represents an integer from 2 to 4.
  • x represents a number from 0 to 100
  • y represents a number from 0 to 100
  • R represents a radical selected from the group consisting of alkyl and alkenyl radicals contain ing from 6 to 22 carbon atoms
  • R represents a radical selected from the group consisting of alkyl and hydroxyalkyl radicals containing from I to 5 carbon atoms
  • X represents an anion said reaction being carried out at a temperature up to 200C.
  • organic aromatic polyisocyanate, thermally reversible blocking agent, and cationic surfactant are selected to furnish a ratio of mols of blocking agent to NCO groups present in the aromatic polyisocyanate of less than 1 and a number of NCO groups of not more than the sum of the hydroxyl groups of the cationic surfactant and mols of blocking agent.
  • thermoly reversible blocking agent is selected from the group consisting of phenol, methylphenol, dimethylphenol, trimethylphenol, ethylphenol, and mixtures thereof.
  • the aromatic polyisocyanate selected from the group consisting of 2,4-toluene diisocyanate', 2,6-toluene diisocyanate; phenylene diisocyanate; methoxyphenylene 2,4- diisocyanate; diphenyl methane 4,4-diisocyanate; 3 methyl-diphenyl methane 4,4'-diisocyanate', diphenyl ether 2,4,

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Polyurethanes Or Polyureas (AREA)
US319745A 1972-12-29 1972-12-29 Wash-durable antistatic agent Expired - Lifetime US3925462A (en)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4104443A (en) * 1977-05-06 1978-08-01 J. P. Stevens & Co., Inc. Antistatic finish for textiles material
US4743266A (en) * 1986-09-09 1988-05-10 The United States Of America As Represented By The Secretary Of Agriculture Process for producing smooth-dry cellulosic fabric with durable softness and dyeability properties
US5387667A (en) * 1990-02-05 1995-02-07 Battelle Memorial Institute Thermally-reversible isocyanate-based polymers
US5470945A (en) * 1990-02-05 1995-11-28 Battelle Memorial Institute Thermally reversible isocyanate-based polymers
US5807957A (en) * 1996-12-23 1998-09-15 Macrochem Corporation Cationic film-forming polymer compositions, and use thereof in topical agents delivery system and method of delivering agents to the skin
US5906822A (en) * 1997-09-25 1999-05-25 Macrochem Corporation Cationic film-forming polymer compositions, and use thereof in topical agents delivery system and method of delivering agents to the skin
FR2834523A1 (fr) * 2002-01-04 2003-07-11 Protex Procede de fabrication d'un agent de traitement destine a ameliorer le pouvoir antistatique d'un support textile
US20060240730A1 (en) * 2005-04-26 2006-10-26 Demott Roy P Wash durable anti-static treatment for textiles and textiles so treated

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0689323B2 (ja) * 1986-06-13 1994-11-09 第一工業製薬株式会社 制電加工剤

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3658717A (en) * 1969-07-07 1972-04-25 Atlas Chem Ind Surfactants for solvent/water systems and textile treating compositions
US3738981A (en) * 1969-12-08 1973-06-12 Ici America Inc Textile treating compositions,process of treating textiles and textile articles

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3658717A (en) * 1969-07-07 1972-04-25 Atlas Chem Ind Surfactants for solvent/water systems and textile treating compositions
US3738981A (en) * 1969-12-08 1973-06-12 Ici America Inc Textile treating compositions,process of treating textiles and textile articles

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4104443A (en) * 1977-05-06 1978-08-01 J. P. Stevens & Co., Inc. Antistatic finish for textiles material
US4743266A (en) * 1986-09-09 1988-05-10 The United States Of America As Represented By The Secretary Of Agriculture Process for producing smooth-dry cellulosic fabric with durable softness and dyeability properties
US5387667A (en) * 1990-02-05 1995-02-07 Battelle Memorial Institute Thermally-reversible isocyanate-based polymers
US5470945A (en) * 1990-02-05 1995-11-28 Battelle Memorial Institute Thermally reversible isocyanate-based polymers
US5807957A (en) * 1996-12-23 1998-09-15 Macrochem Corporation Cationic film-forming polymer compositions, and use thereof in topical agents delivery system and method of delivering agents to the skin
US5906822A (en) * 1997-09-25 1999-05-25 Macrochem Corporation Cationic film-forming polymer compositions, and use thereof in topical agents delivery system and method of delivering agents to the skin
FR2834523A1 (fr) * 2002-01-04 2003-07-11 Protex Procede de fabrication d'un agent de traitement destine a ameliorer le pouvoir antistatique d'un support textile
US20060240730A1 (en) * 2005-04-26 2006-10-26 Demott Roy P Wash durable anti-static treatment for textiles and textiles so treated

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JPS4995000A (US20100268047A1-20101021-C00003.png) 1974-09-09
JPS5239480B2 (US20100268047A1-20101021-C00003.png) 1977-10-05

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